2-Bromopropane → 3-(2,6-dichlorophenyl)-1-isopropyl-7-methylthio-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 1858224Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14]([S:19][CH3:20])=[N:15][CH:16]=2)[NH:11][C:10]1=[O:21].[H-].[Na+].Br[CH:25]([CH3:27])[CH3:26]>CN(C)C=O>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14]([S:19][CH3:20])=[N:15][CH:16]=2)[N:11]([CH:25]([CH3:27])[CH3:26])[C:10]1=[O:21]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution, cooled in ice, of 100 mg (0.27 mmol) of 3-(2,6-dichlorophenyl)-7-methylthio-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one in 6 ml of dimethylformamide was treated with 13 mg (0.33 mmol) of sodium hydride (60% w/w). After 30 minutes the mixture was treated with 0.03 ml (0.3 mmol) of 2-bromopropane and then heated to 90° C. for 2 hours, cooled and left to stand for 3 days. The mixture was evaporated and the residue was treated with 30 ml of dichloromethane and 30 ml of water. The phases were separated and the organic phase was washed with 30 ml of water, dried over magnesium sulfate, filtered and evaporated to give 60 mg (54%) of 3-(2,6-dichlorophenyl)-1-isopropyl-7-methylthio-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one as a yellow solid. [Mass spectrum (ESI) MH+ =383].

Workup

temperaturecooled
waitleft
customThe mixture was evaporated
additionthe residue was treated with 30 ml of dichloromethane and 30 ml of water
customThe phases were separated
washthe organic phase was washed with 30 ml of water
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-83d78f0cf0e14b23852325dbc75257c6
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150373

Reaction notes

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